Potassium Hydroxide → 4-(2-carboxyethyl)-3-methyl-5-(5-bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26](=[O:31])[CH2:25]2.[OH-].[K+]>N1CCCCC1.C(O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:19]=[C:25]1[C:24]2[C:28](=[CH:29][CH:30]=[C:22]([Br:21])[CH:23]=2)[NH:27][C:26]1=[O:31])([OH:16])=[O:15]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 5-formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (281 mg), 5-bromo-2-oxindole (220 mg), and piperidine (2 drops) in ethanol (2 mL) was stirred at 90° C. for 2 hours. Potassium hydroxide (537 mg) was added and the temperature was increased to 95° C. for 1 hour. The reaction mixture was cooled and concentrated. The residue was dissolved into water and acidified with 2 N hydrochloric acid to pH 2. The precipitate that formed was filtered, washed with water and dried in a vacuum oven overnight to give 411 mg (98%) of 4-(2-carboxyethyl)-3-methyl-5-(5-bromo-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid.
Workup
- temperaturethe temperature was increased to 95° C. for 1 hour
- temperatureThe reaction mixture was cooled
- concentrationconcentrated
- dissolutionThe residue was dissolved into water
- customThe precipitate that formed
- filtrationwas filtered
- washwashed with water
- customdried in a vacuum oven overnight
Sources & evidence
- ORD record
- ord-8950a481443e474fa2bc0ce82212f716
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855730B2
Reaction notes
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